It’s hard to imagine our favorite celebrities ever looking or feeling awkward. The way they gracefully conduct themselves on the red carpet and make sure they’re always looking their best. But we were all young once, as this article will explore!
Celebrities have shared how they used to look during their awkward years – something we can all relate to! Read on to see the comparisons from when they were young and where they are today. Some of these transformations are wild…
This smooth charmer was always dashing – even if he sported a mullet in his early days! Pitt’s prom was at Kickapoo High School in Missouri – a full 10 years before his Hollywood breakthrough in Thelma and Louise in 1991.
Today, the star is worth a massive $250 million, although we can expect that to decrease while he pays for his divorce with Angelina Jolie. He can next be seen starring opposite Leonardo DiCaprio in Quentin Tarantino’s new film.
This Die Hard star looks pretty different to how we know him today! Bruce Willis was initially held back by a stutter, but he turned to performance to overcome his speech difficulties.
Today, he is 62 (with a lot less hair) and one of the biggest stars on the planet. He has starred in over 80 movies, helping him build up a net worth of about $180 million. Here he is with a prom date – we bet he had no idea what fame would come!
Lindsay Lohan was basically a normal teen in New York when this photo was taken at her freshman year homecoming. Despite starring in The Parent Trap, the actress had a quiet upbringing outside the public eye until 2003’s Freaky Friday.
Now 31, Lohan spent some time dating Russian real estate empire-heir Egor Tarabasov before calling it quits. She has had man ups and downs in her career, mainly due to alcohol and substance abuse. Here, we can see her youthful innocence.
Before she was the Hollywood icon she is today, Meryl Streep was just your average girl. Today, the 69-year-old is one of three people to ever win three Oscars for acting – after a record 21 nominations!
Before this, she was just your regular New Jersey girl who enjoyed the more calming and relaxing parts of life! Now, Streep’s time is taken up with prestigious award ceremonies around the world. What is your favorite Meryl Streep role?
Everyone can look awkward at times – even the
Today, Beyonce is the glamorous idol everyone knows and loves – and is worth a whopping $500 million! It goes to show that we can all look amazing with a new style guide and wardrobe – although it helps when you have some millions!
Before his time on SNL, Fallon was just your everyday awkward teenager. Here, we can see him at prom looking geeky and pasty. The only thing that’s really changed is his skin tone, but audiences seem to love his awkward and geeky persona.
Today, he is the host of The Tonight Show and worth a whopping $45 million. We can see he hasn’t outgrown his boyish charms, attracting audiences of millions each night. Do you like his show?
If there’s ever a case of the Ugly Duckling, this is it! John Krasinski rose to fame as the geeky Jim in The
Krasinski showed us his filmmaking abilities with the 2018 horror film A Quiet Place, which he starred in opposite his wife, Emily Blunt. What do think of his beard?
Does anyone look as awkward as Ellen? The successful talk show host shared this picture – and the dress itself! – on her show. The 1970s fashion choice hasn’t exactly aged well – nor has the fact that she attending prom with a man.
Today, Ellen is about to turn 61 and celebrate with her wife, Portia De Rossi, to whom she has been married since 2013. She has been a good sport about this awkward photo and even recreated it in 2005 on her show – with her actual prom date!
We don’t need to travel too far back in time to unearth a picture of Harry Styles at prom! The 24-year-old rose to fame in 2010 as a member of One Direction and has achieved success as a solo artist, too.
Today, he is worth a massive $50 million – not bad for a kid in his early 20s! Here he is posing for a high school prom just a few months before he would audition for The X Factor – and his life would change forever!
Courtney Cox started her career in the 1990s as a model with her big break starring in the Bruce Springsteen video, Dancing in the Dark. Today, the Friends star is worth a huge $88 million and lives a pretty different life than her teenage years.
Here she is looking very different in her prom outfit – with a large bouquet of flowers to match! She looks very different from her on-screen character, Monica, who attended prom somewhat overweight.
She announced that they secretly married in 2017, although it didn’t last. The prom outfit is amazing and there isn’t a shred of awkwardness about it – it appears she was born to entertain!
This rapper has never looked more serious! Here is Snoop on his prom looking rather dashing, although we know he prefers the relaxed gear today. Calvin Broadus, as he is known legally, is worth a huge $135 million today so pretty much wears whatever he wants!
It was only shortly after this photo was taken that Dogg was discovered by Dr. Dre – and the collaboration between them proved tight. Today, he is one of the biggest rappers in the world.
Robin Wright has garnered fans across the world for her performance as Jenny in Forrest Gump and as Claire Underwood in House of Cards. Here she is looking young and glowing as a teenager posing for prom.
Today, the 52-year-old is keeping busy in the DCEU as a warrior in the Wonder Woman franchise. We love the vintage look that Wright has here, and her long hair is a contrast to many of the characters she plays on TV. Wright can next be seen in Wonder Woman 1984 next year.
A quick glance at this image and it’s pretty obvious that Will Ferrell has always been a comedian! Here he is at his prom wearing his very own tiara! The 51-year-old rose to fame as a writer and performer on SNL before appearing in classic films like Elf, Anchorman, and Step-Brothers.
We love that the actor clearly always had a spark for comedy and hasn’t lost it over the years! His most recent film, Holmes and Watson was not met with the critical acclaim he is used to.
Underwood was born in Oklahoma, something painfully apparent in this senior prom photo from 2001. She had already been singing in local bars and venues for a few years, but it was her stint on American Idol in 2004 which would launch her to worldwide fame.
To date, the country star has won seven Grammys and sold tens of millions of records – and looks better than ever! She is worth a whopping $85 million and doesn’t need to worry about looking great.
This Kardashian grew up in the spotlight, so we can all remember her prom night! She accompanied Albert to Rio Americano High School in 2017, along with her friend Jordyn Woods, after his date had ditched him. Jenner was homeschooled so never went to her own prom.
According to reports, the highschooler became very popular after turning up with this superstar on his arm! Today, the reality star is worth a whopping $300 million, making her pretty desirable to young men everywhere!
Rachel Green had some bad flashbacks to prom on Friends, and it appears that Jennifer Aniston had no problem acting them! Twenty years later and Aniston is looking as glamorous as ever as she struts herself down red carpets around the world.
It helps that the sitcom sensation earns 2% from all Friends syndication – so we can expect her to pamper herself! Today, Jennifer Aniston appears on the big screen in films such as Horrible Bosses, We’re The Millers, and Netflix’s Dumplin’.
Natalie Portman became a household name after she appeared in Star Wars: Episode 1 – The Phantom Menace. She played Padme Amidala while still in high school, and it launched her career! Today she is worth a huge $60 million and has appeared in films like Garden State.
On top of that, she has received a 2018 Genesis Prize Award given by Israel to Jewish people for excellence in their industry. Her prom photo shows a more awkward young child – something she would grow out of!
This Jersey Shore star has shown she’s always known how to be glamorous. All we need to do is look at the reality star’s prom dress. This superstar has since appeared on another show with her friend Jenni “Jwoww” Farley, as well as a home renovation show with her husband Jionni.
Have you seen her on your screen recently? The 30-year-old star is now worth a massive $4 million, and is as glorious as ever! We look forward to seeing what’s next from the star.
Everyone’s favorite funny girl Amy Poehler started acting professionally in 1998 with the sketch comedy TV show, Upright Citizens Brigade. Today, she is best known for her performances in Parks and Recreation and Inside Out.
As a teen, she looked awkward (but hilarious) in a fluffy prom dress that proved a little too large! Nonetheless, the actress blossomed into a beautiful blonde star who makes millions of people laugh each week. Did you watch her as Leslie Knope?
Blake Lively’s career started when she was ast in The Sisterhood of the Traveling Pants as a teenager. Her breakout role was as Serena in the wildly-popular Gossip Girl and The Green Lantern, where she would meet her future husband, Ryan Reynolds.
Here she is looking like a humble and awkward teen at her prom before developing into the gorgeous celebrity we know today! We think her hair looks much better today!
This photo of Britney was taken in 1997, just a few months before she would shoot the famous Baby One More Time music video. Her freshman single would go on to propel her to worldwide fame and acclaim, launching a career still alive 20 years later.
Despite her infamous breakdown in 2007, Britney has proven to everyone how to overcome troubles in your personal life. Today, she is more glamorous than ever – and worth an impressive $215 million.
Talk about a 1990s look! Here, we can see the Twilight star sprouting spikes from his head as he prepares for from. Today, Taylor Lautner has been pretty quiet in Hollywood probably relaxing with the fortune he made along the way.
His first role was in 2001’s Shadow Fury and has since gone on to make a $40 million fortune. The 26-year-old Michigan local was last seen in 2017’s Scream Queens. He has no upcoming projects – would you like to see him return to the big screen?
Few men embody the 1990s as much as Justin Timberlake. Whether it’s denim suits or pasta hair, the man was certainly iconic when he was a boy. We can see that boyish charm on full display here, as he poses with a cheeky grin and curly hair.
Now 37, Timberlake has blossomed into the charming performer we know today. Today he continues a successful solo career outside of his NSYNC roots and shares a child with his wife, Jessica Biel.
The best part of this young Matthew McConaughey photo is how humble and modest he looks. It doesn’t look as if he knows what fame and fortune he would one day earn. This prom photo surfaced soon after McConaughey won an Oscar for Best Actor for his part in Dallas Buyers Club.
He played a rodeo cowboy who is diagnosed with AIDS in the mid-’80s. This charming actor didn’t need to dig too deep to find a southern drawl – he’s originally from Texas.
Her parents are Michael Jackson and Debbie Rowe, and he would be so proud of his daughter if he got the chance to see how lovely she has become! At only 20, Paris has already followed in her father’s footsteps and entered the music industry.
Here she is with her prom date, sporting an impressive blue head of hair. Jackson is attracted to both men and women but doesn’t identify as bisexual. She remains open-minded to any and all relationships.
This America’s Next Top Model host has always had the modeling abilities, as demonstrated in her prom photo. Banks was discovered at just 15 years of age, which explains the incredible pose she’s striking in this shot. Now 44, the model is worth $90 million, which she uses to benefit charities.
This includes a scholarship for African-American girls in her name at her school Immaculate Heart High School. Find out over the page which celebrity is looking particularly awkward…
Before her Hannah Montana days, Miley Cyrus was just your ordinary girl. Thanks to her father’s success, she could afford this orange beauty – although her awkwardness is still on display! We don’t know much about the guy who accompanied her, but one thing’s pretty certain: many men would kill to be in his place!
Today, Cyrus is a global superstar who just married her longtime boyfriend, Liam Hemsworth. We bet the guy here is kicking himself for not holding onto this date!
Here’s T-Swift pictured at her prom, only a few months before she would reach worldwide fame. The young singer-songwriter actually spent some of her younger years being home-schooled to accommodate her early Nashville fame.
She is now 28 and has shown not only to be a talented musician but a shrewd entrepreneur as well! She launched her own ticket sales site in 2017 – the “Taylor Swift Tix” site. It gives fans a bigger chance of buying concert tickets if they also buy a copy of her album.
Clooney might be one of Hollywood’s most dashing men today, but once upon a time, he was just your average Kentucky kid. Amazingly, he doesn’t appear to have aged much, aside from sprouting a silver head of hair.
Here he is a teenager with a female friend – who could have guessed he would grow up to be worth more than $500 million? Even though he looks a bit awkward, you can still see